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ChemicalBook CAS DataBase List 5-CHLORO-1-METHYL-1H-INDOLE-2-CARBOXYLIC ACID
59908-47-3

5-CHLORO-1-METHYL-1H-INDOLE-2-CARBOXYLIC ACID synthesis

6synthesis methods
methyl 5-chloro-1-methyl-1H-indole-2-carboxylate

148356-79-0

5-CHLORO-1-METHYL-1H-INDOLE-2-CARBOXYLIC ACID

59908-47-3

Step 2: Synthesis of 5-chloro-1-methyl-1H-indole-2-carboxylic acid (43.2) To a THF solution (10 mL) of methyl 5-chloro-1-methyl-1H-indole-2-carboxylate (43.1, 224 mg) was added an aqueous solution (2 mL) of LiOH (36 mg, 1.5 mmol). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the solvent was removed under reduced pressure and the residue was dissolved in 1N aqueous hydrochloric acid solution (10 mL). The resulting suspension was allowed to stand for 10 minutes, then filtered through filter paper, collected as a solid and dried under vacuum to afford 163 mg (77.6% yield) of 5-chloro-1-methyl-1H-indole-2-carboxylic acid (43.2) as a beige powder.

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Yield:59908-47-3 94%

Reaction Conditions:

with sodium hydroxide in ethanol at 50; for 0.5 h;

Steps:

1.2 Preparation of 5-chloro-1-methyl-1H-indole-2-carboxylic acid

77 mg (0.34 mmol) of the compound prepared in the above step 1 was dissolved in ethanol, 2M sodium hydroxide was added, and the mixture was stirred at 50 ° C for 30 minutes. After completion of the reaction, the reaction mixture was extracted with 50 ml of ethyl acetate, washed with 4N hydrochloric acid and water, and dried over anhydrous sodium sulfate.And concentrated under reduced pressure to obtain 67 mg (0.32 mmol) of the title compound as white solid in 94% yield.

References:

KR101725451,2017,B1 Location in patent:Paragraph 0294; 0301-0303